Dares Beach Vacation Rentals from CA $376: Short-Term Rentals for 2026

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Our top choices for Dares Beach vacation rentals

A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

1. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick

Sean B.

CA $561 total

includes taxes & fees

Nov 20 - Nov 21

2. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Ben W.

CA $567 total

includes taxes & fees

Dec 7 - Dec 8

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

3. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

CA $423 total

includes taxes & fees

Nov 12 - Nov 13

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

4. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

CA $442 total

includes taxes & fees

Nov 12 - Nov 13

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

5. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict

ed r.

CA $376 total

includes taxes & fees

Nov 12 - Nov 13

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

CA $346 total

includes taxes & fees

Nov 17 - Nov 18

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

7. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Sarah

CA $645 total

includes taxes & fees

Nov 16 - Nov 17

8. Plum Point Cottage #17

Huntingtown

CA $645 total

includes taxes & fees

Nov 12 - Nov 13

9. Plum Point Cottage #15

Maryland

CA $802 total

includes taxes & fees

Nov 12 - Nov 13

Three Adirondack chairs facing a beach with a clear view of the ocean.

10. Plum Point Cottage #14

Huntingtown

Yonnick H.

CA $762 total

includes taxes & fees

Nov 12 - Nov 13

A lakeside view with chairs and a table, a rainbow, and trees.

11. Bright and airy waterfront getaway

Benedict

George

CA $516 total

includes taxes & fees

Nov 12 - Nov 13

A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

12. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

CA $418 total

includes taxes & fees

Nov 16 - Nov 17

A house with a yellow door and a window with a lamp outside.

13. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

CA $462 total

includes taxes & fees

Nov 15 - Nov 16

14. Just a getaway piece of property

Mechanicsville

David L.

CA $307 total

includes taxes & fees

Nov 15 - Nov 16

A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

15. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

CA $367 total

includes taxes & fees

Nov 13 - Nov 14

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

16. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

CA $616 total

includes taxes & fees

Nov 13 - Nov 14

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

17. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

CA $627 total

includes taxes & fees

Nov 12 - Nov 13

A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

Tanya S.

CA $1,530 total

includes taxes & fees

Nov 12 - Nov 13

A pathway lined with trees and lights leading to a wooden building with a visible window.

19. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lusby

Anonymous traveller

CA $1,157 total

includes taxes & fees

Nov 17 - Nov 18

A deck with outdoor furniture, a red door, and a house with windows.

20. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"

Jenny A.

CA $505 total

includes taxes & fees

Nov 15 - Nov 16

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Top Dares Beach Hotel Reviews

Spark by Hilton California Lexington Park

10/10 Excellent

"Courteous staff, well run facility."

Rod 'N' Reel Resort

8/10 Good

"Our stay was for several days. The property is very well maintained, and great views of Chesapeake Bay. Booking through Expedia is the best decision because the daily rack rate is far higher. There is onsite uniformed security. There are an abundance of handicapped parking and a parking garage. We ate at the property restaurants for convenience, the food was okay, seemed a bit more expensive than the surrounding area restaurants. It’s to be expected. Our biggest concern was housekeeping. We were not told at check-in that room cleaning is every other day if your stay is multiple days, which we did. You have to request daily cleaning at check-in so a negative. We contacted the front desk to adjust the cleaning to daily but it didn’t happen so we tracked down housekeeping and had our towels changed and and shower gel replaced as it was empty. We were in the old building, we could hear people speaking in adjoining rooms and hallways. We had a a good laugh at some of the conversations. We gave the casino a try it is very well maintained. All in all it is a very nice property just a few misses on execution."

Find out more about Dares Beach

Everything you need to know about Dares Beach vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dares Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dares Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dares Beach vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dares Beach. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dares Beach vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dares Beach vacation rentals we have selected for you start as low as CA $376 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dares Beach rentals

At Expedia, we put the best Dares Beach vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Dares Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dares Beach vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dares Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Dares Beach?

Yes, you can find vacation rentals near well known points of interest in Dares Beach, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Dares Beach?

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels: This vacation home rental outside of Dares Beach offers a balcony, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Dares Beach?

Choose from 3 Expedia vacation rentals in Dares Beach for a memorable vacation.

What can I see and do in Dares Beach?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Breezy Point Beach and Matoaka Beach.

What are vacation rentals like in Dares Beach?

Vacation rentals are private properties you can stay in for a short or long stay in Dares Beach. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Dares Beach vacation rentals

1. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

2. Family Beach House: Spacious Deck, Grill & Views

3. Beachside Oasis with Beach Passes & King Suite by A Haven Away

4. The Cozy Crab- Your Charming Haven in Lovely North Beach!

5. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays